This study uses a phenomenological approach to examine how Latino male students at community colleges engage with their male peers. The analysis utilizes a male gender role conflict (MGRC) framework and employs cultural conceptions of masculinity, specifically machismo and caballerismo. Practitioners and researchers might leverage positive aspects of masculinity associated with caballerismo to help men succeed academically, while promoting reflection on and interrogation of aspects of masculinity that might lead to negative educational outcomes.